Water → [2-(3-Bromofuran-2-yl)-ethoxy]-tert-butyldimethylsilane

HRID 1778360Notes

Reaction equation

HRID 1778360 reaction equation
FC(F)(F)S([O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8])(=O)=O.[Br:16][C:17]1[CH:21]=[CH:20][O:19][C:18]=1[CH2:22][CH2:23]O.N1C=CC=CC=1.O>C(Cl)Cl>[Br:16][C:17]1[CH:21]=[CH:20][O:19][C:18]=1[CH2:22][CH2:23][O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 639438362-(3-Bromofuran-2-yl)ethan-1-ol2×

Product 1

HCID 66692617[2-(3-Bromofuran-2-yl)-ethoxy]-tert-butyldimethylsilaneYield 84.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyldimethylsilyl trifluoromethanesulfonate (4.47 g) was added to a solution of 2-(3-bromofuran-2-yl)-ethanol (Intermediate 35, 2.94 g) and pyridine (2.43 g) in DCM (40 mL) and the mixture was stirred for 90 minutes. Water was added and the organic layer was separated, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of DCM and cyclohexane with a gradient of 0-25% to give [2-(3-bromo-furan-2-yl)-ethoxy]-tert-butyldimethylsilane (3.98 g) as a colourless oil. The material was used without further characterisation.

Workup

  1. customthe organic layer was separated
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness
  5. customthe residue was purified by chromatography on silica
  6. washeluting with a mixture of DCM and cyclohexane with a gradient of 0-25%

Sources & evidence

ORD record
ord-b7f9937529a349f88f226611d4357716
Source dataset
uspto-grants-2016_02
Patent number
US09266896B2

Reaction notes

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